Acylamino symmetrical triazines



United States Patent" 6 The present application is a division ofapplication Serial No. 89,930, filed February 17, 1961, now US. PatentNo. 3,195,998. I

The present invention relates to new triazine derivatives with valuableherbicidal properties, as wellas processes for their preparation andtheir use for inhibiting plant growth.

It has been found that symmetrical triazine derivatives of thegeneralformula I I COR1 x- N v in which Hal signifies chlorine, bromineor fluorine,

R signifies hydrogen or a low molecular alkyl or alkenyl radical, Rsignifies hydrogen or a low molecular alkyl, alkenyl or alkoxyalkylradical, and X signifies chlorine, bromine or fluorine or an radical inwhich R is a low molecular alkyl, alkenyl or alkoxyalkyl radical or theradical of a low molecular saturated or unsaturated fatty acid and R isa radical corresponding to the definition for R possess an excellentherbicidal activity and, if X is a halogen atom, may also befungicidally active.

For the preparation of the above defined new triazine derivatives, acyanuric acid trihalide such as cyanuric chloride, cyanuric bromide orcyanuric fluoride, is reacted in an inert organic solvent with one ortwo mol of an alkali metal salt of an acylamide of the general formulaB2 (II) in which R, and R have the meaning given above, or is reactedsuccessively with one mol each of alkali metal salts of different suchacylamides. Suitable solvents are, for example, aliphatic and aromatichydrocarbons or ethers. The alkali metal salts of the acylamides of thegeneral Formula II, i.e. the salts of lithium, sodium and potassium, maybe prepared by known methods, for example by reacting the correspondingacylamides with lithium amide or with sodium in inert organic solventssuch as, for example, toluene. After preparation of the acylamide salts,the reac-tion with, for example cyanuric chloride, may be carried outdirectly after in the same solvent without isolation of the salts.

If the reaction is carried out with one mol of an acylamide salt, it isadvantageous to effect the reaction at low temperatures, for example, at,15 to If two mol of an acylamide salt are reacted, it is advantageous 3244,7 l 2 Patented Apr. 5, 1965 to replace the second halogen atom bythe acylamino radical at somewhat higher temperature, for example at3040' C.

Suitable starting substances of the general Formula II are, for example,the sodium, potassium and lithium salts of the following acylamides:N-ethyl-acetamide, N-methylac'etamide, propionylamide,N-ethyl-propionylamide, N- butylacetamide, N ethyl trimethylacetamide, Nallylacetamide, N-(p-methoxyethyl)-acetamide,N-(v-methoxypropyD-acetamide and N-methyl formamide etc.

Conforming to a modification of this process, the cyanuric acidtrihalide may be reacted successively and in any order with 1 mol of anacylamide alkali salt of the general Formula II and, in the presence ofan acid binding agent, with one mol of an amine of the general formula(III) N I Hal J 1 4 with one mol of an alkali metal salt of an acylamideof the general Formula II in an inert organic solvent.

According to a second process, monoacylated halogenamino symmetricaltriazines corresponding to the general Formula I and having the morespecific general formula in which Hal, R and R have the meanings givenabove and X represents a halogen atom or a radical in which R representsa low molecular alkyl, alkenyl or alkoxyalkyl radical and R is definedas above, may be prepared by acylating under heating in an inert organicsolvent, preferably boiling between and C., a compound of the generalformula lll'al in which Hal, R and X have the above meanings, with areactive functional derivative of a carboxylic acid of the generalformula HOOCR (VII) in which R has the meaning given above, especiallywith an excess of an anhydride of such an acid. In order to obtain goodyields in this process, the reaction conditions and the reaction period,preferably between 1 and hours, are so chosen that monoacylation takesplace in the starting substances without the reaction simultaneouslygoing too far with hydrolysis of the halogen attached to the nucleus bythe acid set free during the acylation. The following anhydrides may beused, .for example, as reac tive functional derivatives of carboxylicacids of the general Formula VII: acetic anhydride, propionic anhydride,

butyric or isobutyric anhydride, as well as the anhydrides of crotonicacid, acrylic acid, methacrylic acid and so on, and also formicacid-acetic acid anhydride as a reactive derivative of formic acid'forintroduction of the formyl radical.

The following may be mentioned as examples of suitable startingsubstances of the general Formula VI:

2,4-dichloro-6-methylamino-1,3,5-triazine, 2,4-dichloro-6-ethylamino-1,3,5-triazine, 2,4-dichloro-6-isopropylamino-1,3,5-triazine,2,4-dichloro-6-butylamino-1,3,5-triazine, 2,4-difluoro-6-ethylamine-1,3,5 -triazine, 2,4-dichloro-6-('y-methoxypropylamino)-1,3,5-triazine,2,4-dibromo-6-isobutylamino-l ,3 ,S-triazine,2,4-dichloro-6-allylamino-1,3,5-triazine, 2-chloro-4,-bis-ethylamino-1,3,5 -triazine, 2-fluore-4,6-bis-ethylamino-1,3 ,S-triazine,2-fiuoro-4,6-bis-isopropylamino-1,3,5-triazine, 2-chloro-4,6-bis-sec.butylamino-l,3,5-triazine, 2-bromo-4,6-bis-methylamino-1,3 ,5 -triazine,2-chloro-4,6-bis-allylamino-l ,3 ,5 -triazine,2-chloro-4-ethylamino-6-isopropylan1ino-1,3,5-triazine,2-chloro-4-diethylamino-6-ethylarnino-1,3,5-triazine,2-chloro-4-n-propylamino-6-isopropylamino-1,3,5-triazine,2-chloro-4-allylamino-o-ethylamino-1,3,5-triazine,2-bromo-4-ethoxyethylamino-6-dimethylamino-1,3 ,5 -triazine,2-chloro-4-ethylamino-6-diallylamino-1,3 ,5 -triazine.

A large part of these starting substances is known, the rest may beprepared by known methods.

As the inert solvents, the following, boiling between 100 and 150", arepreferably used: n-octane, methylcyclohexane, petrol fractions, toluene,xylenes, ethylbenzene, dioutyl ether, anisole, dioxan, acetal,methylisobutyl ketone, butyl acetate, chlorobenzene, tetrachloroethane,tetrachloroethylene, nitromethane, 1,3-propane dichlorideand Z-hexanone.

According to a modification of this process, compounds of the generalFormula I are obtained when the monoacylation of the compound of thegeneral Formula VI is effected by reacting it with a low molecularaliphatic ketene, especially with carbomethylene, in the presence of acatalyst such as little amounts of a mineral acid.

Particularly elfective herbicidal compositions according to thisinvention comprise as an active herbicide, a triazine derivative of thegeneral Formula I wherein Hal is a chlorine, bromine or fluorine atom; Ris hydrogen, lower alkyl or lower alkenyl, R is hydrogen, lower alkyl,lower alkenyl or lower alkoxylower alkyl, and X is chlorine, bromine,fluorine or R being lower alkyl, lower alkenyl, lower alkoxy-lower alkylor lower unsaturated or lower saturated acyl and R having the samemeaning as R By the term lower is meant radicals containing 1-4 carbonatoms. Examples of lower alkenyl radicals are allyl, vinyl, propylideneetc. Lower alkoxy-lower alkyl radicals are, for example, B-ethoxyethyl,methoxymethyl, 'y-rnethoxypropyl etc. Examples of unsaturated acylradicals are crotonyl acryl, dimethylacryl etc.

It is not desired to restrict the new triazine compounds to only thespecific ones shown in the following examples. Any compounds fallingunder the generic compound are applicable. Further exemplification ofcompounds obtainable according to the procedures found in Example 1 are:

2-chloro4,6-bis- (N-acetyl-vinylamino) -1 ,3 ,5 -triazine,

2-chloro-4,6-bis (N-acetyl-propylideneamino) -1 ,3 ,5 -triazine,

2-chloro-4,6-bis-(N acetyl-fi-ethoxyethylamino) -1,3 ,5 -triazine,

2-chloro-4,6-bis-(N-acetyl-methoxymethylamino)-1,3,5-

triazine,

2-chloro-4, 6-bis- (N-acrylyl-ethylamino) -1 ,3,5-trlazine,

2-chloro-4,6-bis- (N-dimethylacrylyl-ethylamino -1,3 ,5-

triazine,

2,4-dichloro-6-(N-acetyl-vinylamino -1,3,5-triazine,

2,4-dichloro-6-(N-acetyl-propylideneamino)-1,3,S-triazine,

2,4-dichloro-6- (N-acetyl-B-ethoxyethylamino) -l ,3 ,5 -triazine,

2,4-dichloro-6- (N-acetyl-methoxymethylamino) -1,3 ,5 -triazine,

2,4-dichloro-6-(N-acrylyl-ethylamino) -1,3,5-triazine,

2,4-dichloro-6-(N-dimethylacrylyl-ethylamino) -1,3 ,5 -triazine,

2-chloro-4,6-bis-(N-acetyl-vinylamino) -1,3,5-triazine,

2-chloro-4,6-bis-(N acetyl-propylideneamino) -1,3 ,S-triazine,

2-chloro-4,6-bis- (N-acetyl-B-ethoxyethylamino) l ,3 ,S-triazine,

2-chloro-4,6-bis-(N-acetyl-methoxymethylamino -1,3 ,5-

triazine,

2 chloro 4,6-bis- (N-acrylyl-ethylamino) -l ,3 ,5 -triazine,

and

2-chloro-4,6-bis-(N-dimethylacrylyl-ethylamino)-1,3 ,5

triazine.

The preparation of the new active substances according to the inventionis illustrated in more detail by the following examples. Parts thereinrepresent parts by weight. The temperatures are given in degreescentigrade.

Example 1 9.2 parts (2 equivalents) of sodium are pulverised at and 1000parts of anhydrous toluene and then 36 parts (2 equivalents) ofN-ethylacetamide dissolved in 500 parts of toluene are dropped in atthis temperature. After the reaction has finished, 38 parts (1equivalent) of cyanuric chloride in 200 parts of toluene are dropped inat -15. The suspension is stirred for 20 hours at 20, then for 23 hoursat 50". After cooling, it is treated with water, the phases areseparated and the organic phase is washed with water, dried with sodiumsulphate and the toluene is distilled ofi. The residue is distilled. The2- chloro-4,6-bis-(N-acetyl-ethylamino) 1,3,5-triazine boils at124-128/0.003 mm.

The following compounds are obtained in a similar way using 2equivalents of acylamide salt and 1 equivalent of cyanuric halide:

2 chloro 4,6-bis-(N-acetyl-n-butylamino)-1,3,5-triazine,,

B.P. 131 /0.0005 mm., 2-chloro-4,6-bis-(N-butyryl-rnethylamino)-1,3,5-triazine,

B.P. /0.002 mm.,

' 2-fiuoro-4,6-bis- (N-acetyl-ethylamino -l,3,5-triazine, B.P.

106115/0.08 mm.,2-chlor0-4,6-bis-(N-crotonyl-ethylamino)-l,3,5-triazine, l

B.P. 155156/0.004 mm.,2-chloro-4,6-bis-(n-formyl-methylarnino)-l,3,5-triazine,2-chloro-4,6-bis- [N-acetyl- ('y-methoxy-propylarnino) ]-.l

3,5-triazine, B.P /0.03 mm. under decomposition,2-chloro-4,6-bis-(N-acetyl-allylamino)-1,3,5-triazine, B.P.

l50-160/0.008 mm. 4

ene are added dropwise at 100 to this mixture.

Example 2 46 parts of lithium amide are suspended in 5000 parts oftoluene. 180 parts ofN-ethylacetamide (1 equivalent) are then addeddropwise to this suspension. The suspension so obtained is heated for 40hours at 110 and then 380 parts of cyanuric chloride (1 equivalent) in2000 parts of toluene are added dropwise at -15. After heating -for 24hours at 40-50", the reaction mixture is cooled,

2,4-dichloro-6-(N-n-butyryl-methylamino) 1,3,5-triazine,

B.P. 108-116/0.01 mm.,

2,4-dichloro-6-(N-formyl-methylamino) 1,3,5-triazine,

2,4-dichloro-6-(N-crotonyl-ethylamino) 1,3,5 triazine,

B.P. 118/0.001 mm., 2,4-dichloro-6-(N-acetyl-allylamino) 1,3,5-triazine,B.P.

102-1 O5/0.004 mm., 2,4-fluoro-6-(N-acetyl-ethylamino) 1,3,5-triazine,B.P.

43-46/0.02 mm., 2,4-dichloro 6 [N-acetyl-('y-methoxypropylamino)]-1,3,5-triazine, B.P. 137140/0.05 mm.

Example 3 To produce an acylamide sodium salt, 23 parts of sodium arepulverised in 3000 parts of toluene and 87 parts of N-ethylacetamidedissolved in 1000 parts of tolu- On completion of the reaction, asolution of 221 parts of the known compound2,4-dichloro-6-diethylamino-1,3,5- triazinein 500 parts of toluene isadded dropwise. After stirring for 24 hours at 60, the reaction mixtureis cooled and the product is worked up as described in Example 1.

The 2 chloro-4-diethylamino-6-(N-acetyl-ethylamino)- 1,3,5-triazineobtained boils at 125 /0.0009 mm. Hg.

Example 4 2,4 dichloro-6-(N-acetyl-ethylamino)-1,3,5-triazine is firstproduced from 1 equivalent of cyanuric chloride and 1 equivalent ofN-cthyl acetamide either as described in Example 2 or on usingpulverised sodium instead of lithium amide. 235 parts of the2,4-dichloro-6-(N-acetylethylamino)-1,3,5-triazine so obtained are thendissolved in 2000 parts of benzene and. a solution of 118 parts ofisopropylamine (excess to bind the hydrochloric acid) in 500 parts ofbenzene is added dropwise to this solution at room temperature. Afterrefluxing for 16 hours, the reaction mixture is filtered, the benzene isdistilled off and the residue is recrystallised from petroleum ether.The 2-chloro-4-isopropylamino 6 (N-acetyl-ethylamino)- 1,3,5-triazine soobtained melts at 9497.

By reacting one mol of an acylamide salt and one mol of an amine of thegeneral Formula III in this or in the other sequence, further compounds,mentioned after Example 5, may be prepared starting from cyanurichalides.

Example 5 100 parts of 2-chloro-4,6-bis-ethylamino-1,3,5-triazine and105 parts of acetic acid anhydride in 500 parts of chloro-benzene arerefluxed for 2 hours. After distilling off half of the solvent,unreacted 2-chloro-4,6-bis-ethylamino-1,3,5-triazine is filtered off hotand the filtrate is concentrated to dryness in vacuo. The crystallineresidue is taken up in 250 parts of acetone; the solution is filteredand, while stirring, poured into 1500 parts of ice water. The2-chloro-4-ethylamino-6- (N-acetyl ethylamino -1 ,3 ,5

- triazine so obtained as colourless precipitate melts at 104- 105 andcan be recrystallisedfrom petroleum ether.

The following compounds are obtained in a similar way:

Example 6 23 parts of 2-chloro-4-diethylamino-6-ethylamino-1,3,5-

triazine and 2 parts of concentrated sulphuric acid are dissolved in 200parts of benzene. For the monoacetylation, carbomethylene (ketene) ingaseous form is introduced into this solution for2 hours at 60. Oncompletion of the reaction, the benzene solution is washed with sodiumcarbonate solution and water and dried over sodium sulphate. Afterdistilling off the benzene, the residue is distilled. The2-chloro-4-diethylamino-6-(N-acetylethylamino)-l,3,5-triazine soobtained boils at 125 under 0.0009 mm. Hg and is identical with thecompound obtained according to Example 3. In the pure form, the compoundis crystalline.

From ketene and 2-chloro-4,6-bis-(methylamino)-1,3,5 triazine withacetone as solvent, 2-chloro-4-methylamino-6-(N-acetylmethylamino)1,3,5-triazine (M.P. 15615 8) is obtained, andfrom ketene and 2-chloro-4,6-bis(ethylamino)-l,3,5-triazine with acetoneas solvent, 2-chloro-4-ethylamino-6-(N-acetyl-ethylamino)-1,3,5-triazine is obtained (M.P.104-105, B.P. l35-138) in an analogous manner.

The compounds of the general Formula I defined at the beginning,mentioned above as well as others, are particularly suitable as activesubstances for weed control agents, both for the selective supressionand destruction of weeds among cultivated plants and for the completedestruction and prevention of undesired plant growth. By weeds are herealso meant unwanted, e.g. formerly grown, cultivated plants. Theabove-defined compounds, moreover, are also suitable as activesubstances for carrying out other inhibiting etfects on plant growth,especially defoliation, e.g. of cotton plants, acceleration of maturityby premature drying, e.g. of potato plants, and also reduction ofsetting of fruit, extension of the harvesting periods and of thestoraoility.

Emulsifying or dispersing agents may beadded to said carriers(especially when in water or when intended for use in water) to ensureproper dispersibility. All forms of application have merely to ensurethat the active substance is finelydistributed. Especially in the totaldestruction of plant growth, in premature drying and in defoliation, theaction canbe intensified by the use of carriers which are themselvesphytotoxic, such as for example, high boiling mineral oil fractions; onthe other hand theselectivity of the growth inhibition generally comesmore clearly into playvduring the use of carriers inert towards plants,e.g. in selective weed killing.

Higher boiling organic liquids such as mineral oil fractions coal taroils as well as vegetable and animal oils, are especially suitable forthe preparation of solutions. In order to facilitate the solution of theactive substances in these liquids, small amounts of organic liquidswith better solvent power and usually of lower boiling point may beadded where necessary, i.e. solvents such as alcohols, for exampleethanol or isopropanol, ketones, for example acetone, butanone or'cyclohexanone, diacetone alcohol, cyclic hydrocarbons, for examplebenzene, toluene or xylene, chlorinated hydrocarbons for exampletetrachloroethane or ethylene chloride, or mixtures of the abovementioned substances.

'In the case of use in aqueous fob-ms, emulsions and dispersions areprimarily concerned. The substances as such or in one of the abovementioned solvents are homogenised in water, preferably by means ofemulsifyring or dispersing agents. As examples of cationic emulsifyingor dispersing agents may be mentioned quaternary ammonium compounds; asexamples of anionic emulsifying agents, soaps, soft soaps, alkali metalsalts of aliphatic long-chain sulphuric acid monoesters,aliphaticaromatic sulphonic acids or long-chain alkoxyacetic acids; andas nonionic emulsifying agents, polyethylene glycol ethers of fattyalcohols or alkylphenols and polycondensation products of ethyleneoxide. On the other hand, liquid or pastelike concentrates consisting ofactive substance, emulsifying agent or dispersing agen-tand if necessarysolvent may also be prepared which are suitable for dilution with water.

Dusts and composition for scattering may be prepared first of all bymixing or grinding together the active substance with a solid carrier.As such carriers may be used talcum, diatomaceous earth, kaolin,bentonite, calcium carbonate, tricalcium phosphate, sand, and alsosawdust, cork powder and other materials of vegetable origin. On theother hand, the substances may also be brought on the carrier by meansof a volatile solvent. By addition of wetting agents, e.g. the abovementioned emulsifying agents, and protective colloids, e.g. sulphitewaste liquor, pulverulen-t preparations and pastes which can besuspended in water may be made usable as sprays.

The various forms of application may be adapted more closely to thepurposes for which they are to be used in the usual way by addition ofsubstances which improve or reduce the distribution and the power ofpenetration into the soil according to the depth of the root of theweeds to be killed. Their biological action can likewise be broadened byaddition of substances with bactericidal or fungicidal properties, forexample, to attain a general sterilisation of the soil or in selectiveweed control to protect the cultivated plants from other harmfulorganisms. Substances which also affect plant growth may be wanted foraccelerating the start of the action such as, for example,3-amino-1,2,4-triazole, or if necessary for broadening the spectrumofherbicidal activity such as, for example, salts of a,adichloropropionicacid. The combination with fertilisers represents in some cases a savingin work and may increase the resistance of the cultivated plants to beprotected.

Examples of typical forms of application are given below:

Example 7 parts of active substance, e.g.2-chloro-4-isopropylamino-6-(N-acetyl ethylamino) 1,3,5 triazine, and 90parts of talcum are ground as finely as possible in a ball mill, a discmill or any other suitable mill. The mixture obtained serves as a dust.

Example 8 20 parts of active substance, e.g. 2-bromo-4ethylamino-6-(N-acetyl-ethylamino)-l,3,5-triazine, are dissolved in a mixture of 48parts of diacetone alcohol, 16 parts of xylene and 16 parts of ananhydrous, high molecular weight condensation product of ethylene oxidewith higher fatty acids. This concentrate may be diluted with water togive emulsions of any desired concentration.

8 Example 9 50-80parts of active substance, e.g.2-chloro-4-ethylamino-6-(N-acetyl-ethylamino)-1,3,5-triazine, are mixedwith 2-5 parts of a wetting agent, e.g. a sulphuric acid ester of analkyl polyglycol ether, 1-5 parts of a protective colloid, e.g. spentsulphite liquor, and 14-44 parts of an inert solid carrier material suchas, for example, kaolin, bentonite, chalk or kieselguhr, and then finelyground in a suitable mill. The wettable powder obtained may be stirredwith water and gives very stable suspensions.

Example 10 10 parts of active substance, e.g. 2-chloro-4-ethylam-ino- 16-(N-propionyl-ethylamino)-1,3,5-triazine, are dissolved in 60-80 partsof a high boiling organic liquid, such. as, for example, coal tar oil,diesel oil or spindle oil, to which are added 30-10 parts of xylene.

Example 11 5-10 parts of active substance, e.g. 2,4-dichl0ro-6-(N-formyl-methylamino)-1,3,5-triazine, are mixed with 90 parts of calcium(=ground limestone) and ground. The product may be used as a scatteringcomposition.

Example 12 amount, e.g. -900 parts, of a possibly water solubleartificial fertiliser such as, for example, ammonium sulhate ure. P aExample 13 50 parts of active substance, e.g. 2-chloro-4,6-bis-(N-acetyl-ethylamino)-1,3,5-triazine, are introduced into 45 parts ofxylene and 5 parts of a mixture of polyethylene oxide condensationproducts and spent sulphite liquor are added. A concentrate for thepreparation of emulsions,

which may be emulsified in water in any proportion, is obtained.

The quantities of active substance required per hectare vary inselective weed control-according to the sensitivity of the weeds, theresistance of the cultivated plants, the time of application, theclimatic conditions and soil conditions, between about 0.25 and 10 kg.per hectare, while for the complete prevention of plant growth 5-20 kg.per hectare have in general to be used. In particular 1 cases the abovequantities may also be exceeded.

Example 14 Seed boxes are filled With earth and the seeds of thefollowing plants were placed in each box: mustard, sugar beet, spinachand cucumber. Immediately after planting the seeds one gramme of2-chloro-4-ethylamino-6- (N-acetyl-ethylamino)-1,3,5-triazine in 100 ml.of water is sprayed per square metre seed box surface, which correspondsto 10 kg. of active substance per hectare. Three weeks after planting,the seedlings of all four types of plants were killed.

Example 15 Various test plants were sown in a freshly prepared bed.Immediately after sowing, 200 ml. of an aqueous preparation of 0.1 g. of2-chloro-4,6-bis-(N-acetyl-ethylamino)-1,3,5-triazine were sprayed persquare metre, which corresponds to a concentration of 1 kg. activesubstance per hectare. After 47 days, it was found that maize remaineduninjured, mustard and flax were only slightly damaged whilst ray grass,sugar beet, luzerne, clover,

chickory and hemp were completely or almost completely killed. In thisconcentration the active substance thus 'has a strongly selectiveaction.

Q Example 16 Some time after the shoots have appeared or after the seedshave been sown, cultivated plants are sprayed with 300 ml. of an aqueouspreparation of 0.1 g. of 2-chloro- 4 ethylamino-6 (N-acetyl-ethylamino)1,3,5 triazine per square metre, which corresponds to a concentration of1 kg. active substance per hectare.

After 48 days, kohlrabi, leeks, maize and vetch remained uninjured,wheat, barley and rape were only slightly damaged whereas beans, clover,carrots and spinach were completely destroyed.

In addition to this strongly selective action on cultivated plants, thisactive substance also had an excellent action on weeds, the seeds ofwhich had germinated naturally from seeds after the cultivated plantshad been sown (species of Mercurialis, Veronica and Umbelliferae). Thegrowth of these weeds was completely inhibited.

In the preparations containing high boiling organic liquids, thosehaving a boiling point range of 140-360 C. have been found suitable. Asset forth in the foregoing, the new triazine derivative can be broughtonto the carrier, i.e. mixed with a carrier, in the form of a volatilesolvent dispersion, e.g. in liquids having a boiling point range of55145 C. (e.g. acetone, benzene, xylene, ethylene trichloride etc.).

What we claim is:

1. Triazine derivatives of the general formula wherein Hal represents amember selected from the group consisting of chlorine, bromine andfluorine,

R represents a member selected from the group consisting of hydrogen,lower alkyl and lower alkenyl,

R represents a member selected from the group consisting of hydrogen,lower alkyl, lower alkenyl and lower alkoxy-lower alkyl,

X represents a member selected from the group consisting of chlorine,bromine, fluorine and in which R is a member selected from the groupconsisting of lower alkyl, lower alkenyl, lower alkoxy-lower alkyl,lower saturated and lower unsaturated acyl and R is the same as R 2. Thecornopund 2 chloro 4,6 bis (N acetylethylamino)-l,3,5-triazine.

3. The compound 2 chloro 4monoisopropylamino-6-(N-acetyl-ethylamino)-1,3,5- tri=azine.

4. The compound 2 chloro 4 monoethylamino-6-(N-propionyl-ethylamino)-1,3,5-triazine.

5. The compound 2-chloro-4-monoethylamino-6-(N-acetyl-ethylamino-1,3,5-triazine.

References Cited by the Examiner UNITED STATES PATENTS 2,273,687 2/1942Bock et a1. 26O249.8

WALTER A. MODANCE, Primary Examiner.

I. M. FORD, Assistant Examiner.

1. TRIAZINE DERIVATIVES OF THE GENERAL FORMULA